Tuckahoe Holiday Rentals

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Holiday Rentals in Tuckahoe

Newly Renovated Southampton Home with Heated Pool

7.6 out of 10, Good, (4)
"Wonderful home. Perfect for family and entertaining. "
Newly Renovated Southampton Home with Heated Pool

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (166)
"Perfect family home"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Beautiful Family Home Nestled In The Heart Of Sagaponack

10.0 out of 10, Exceptional, (30)
"Great space and location. We loved the house and enjoyed our stay. "
Beautiful Family Home Nestled In The Heart Of Sagaponack

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

9.6 out of 10, Exceptional, (95)
"We had an absolutely amazing time at Brian’s home. The pool was beautiful and the hot tub was perfect! The home was spacious and the deck was perfect for grilling and hanging outside. This home was great for a big family to get together and have a relaxing fun weekend together. We would definitely recommend and would love to go back ! "
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Autumn in the Hamptons! Pumpkin picking, apple picking, wine tasting and more!

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Autumn in the Hamptons! Pumpkin picking, apple picking, wine tasting and more!

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (171)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country

Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

Contemporary home, newly built, heated pool and hot tub, large deck and...

9.4 out of 10, Exceptional, (8)
"This house was great! Exactly as pictured. Only callout is the outdoor furniture by the pool needs a really good spray down/wash. Everything else was absolutely great!!"
Contemporary home, newly built, heated pool and hot tub, large deck and...

Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

10.0 out of 10, Exceptional, (78)
"Second time staying here, great house right on the water. Owners are extremely responsive and helpful"
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets

Private 2.1 acre gated home with heated pool and tennis & pickleball court

10.0 out of 10, Exceptional, (17)
"With a baby we needed a place with enough entertainment, so we didn’t have to go out much. This place has ALL of that and more. We loved it. We cooked, grilled, swam, played tennis, pickleball, ping pong, pool; all at the house. It was perfect."
Private 2.1 acre gated home with heated pool and tennis & pickleball court

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (22)
"We enjoyed our stay. The location was great and the owner was available for questions. "
Location and views! Located directly on Shinnecock Bay!

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

10.0 out of 10, Exceptional, (11)
"The house is very nice. Very updated and clean. Best bathrooms in any house we have stayed in. The kitchen was large and very nice. Backyard is nice and private with plenty of room. My only issue is that there are so many trees that it blocks a lot of the sun. The pool is in the shade most of the time. In the hot summer it might be great to get some shade but our week was in the low 70's and we could have used a little more sun on the pool. House is in a good location, close to town and the...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

9.8 out of 10, Exceptional, (25)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Tuckahoe you may be interested in

The Atlantic Hotel

2.5 star property
7.0 out of 10, Good, (822)
"Was great property for the cost. Our room was not serviced so we ran out of towels and toilet paper. Would have been better if people in the room next to us hadn't been smoking excessively and seeping into our suite."
The price is AU$210
includes taxes & fees
27 Nov - 28 Nov
The Atlantic Hotel

Newly Renovated Southampton Home with Heated Pool

7.6 out of 10, Good, (4)
"Wonderful home. Perfect for family and entertaining. "
Newly Renovated Southampton Home with Heated Pool

Residence Inn by Marriott New York Long Island East End

3.0 star property
9.2 out of 10, Wonderful, (851)
"All the staff was very nice and helpful Very clean hotel. Price was great "
The price is AU$207
includes taxes & fees
3 Dec - 4 Dec
Residence Inn by Marriott New York Long Island East End
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Tuckahoe?

Yes, there are holiday rentals close to the most popular sights in Tuckahoe, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Tuckahoe speak positively about the beaches and coffee shops in this destination. Make sure you have time to check out the golf courses and monuments during your trip.

What are some of the best holiday rentals that Tuckahoe has to offer?

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr: This holiday home rental outside of Tuckahoe offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Tuckahoe?

Expedia has 53 holiday rentals for your stay in Tuckahoe.

What can I see and do in Tuckahoe?

While exploring the area, visit family-friendly sights like Railroad Museum of Long Island, or get outside and enjoy nature at The Hamptons Beaches. Other places in town to visit include Shinnecock Hills Golf Course and Southampton Golf Range.

What are holiday rentals like in Tuckahoe?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Tuckahoe. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family getaway.